Hydrochloric Acid → 2,2,3,3-Tetrafluoro-1-Hydroxy-4-n-Propylbicyclo[2.2.2]octane

HRID 1644129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1644129
[F:1][C:2]1([F:23])[C:7]([F:9])([F:8])[C:6]2([CH2:12][CH2:13][CH3:14])[CH2:10][CH2:11][C:3]1([O:15]C(CCCCC)=O)[CH2:4][CH2:5]2.[OH-].[K+].O.Cl>C(OCC)(=O)C.C(O)C>[F:1][C:2]1([F:23])[C:7]([F:9])([F:8])[C:6]2([CH2:12][CH2:13][CH3:14])[CH2:5][CH2:4][C:3]1([OH:15])[CH2:11][CH2:10]2

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 594810472,2,3,3-Tetrafluoro-1-Pentylcarbonyloxy-4-n-Propylbicyclo[2.2.2]octane

Produkt 1

HCID 594809982,2,3,3-Tetrafluoro-1-Hydroxy-4-n-Propylbicyclo[2.2.2]octane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 2,2,3,3-tetrafluoro-1-pentylcarbonyloxy-4-n-propylbicyclo[2.2.2]octane (11) (0.30 g), potassium hydroxide (0.10 g), water (0.5 mL), and ethanol (2.0 mL) was stirred at 70° C. for 20 minutes. The mixture was neutralized with hydrochloric acid, added with ethyl acetate (30 mL), and the organic layer was washed with aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then vaporized off under reduced pressure, to thereby obtain a crude product. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3:1), to thereby obtain 2,2,3,3-tetrafluoro-1-hydroxy-4-n-propylbicyclo[2.2.2]octane (12) (yield=0.20 g, yield ratio=94%) as a colorless clear solid.

Aufarbeitung

  1. washthe organic layer was washed with aqueous sodium hydrogen carbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-83599814ad434dfebc9a69f2d48372ba
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124196B2

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